Methanol → Methyl 5-bromo-2,3-difluoro-4-(trimethylsilyl)benzoate

Reaction equation

S(=O)(=O)(O)O.[Br:6][C:7]1[C:8]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[C:9]([F:17])[C:10]([F:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].[CH3:22]O>>[Br:6][C:7]1[C:8]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[C:9]([F:17])[C:10]([F:16])=[C:11]([CH:15]=1)[C:12]([O:14][CH3:22])=[O:13]

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 585380595-Bromo-2,3-difluoro-4-(trimethylsilyl)benzoic acid

Product 1

HCID 58538053Methyl 5-bromo-2,3-difluoro-4-(trimethylsilyl)benzoate

Procedure

Sulfuric acid (1.88 mL, 22.3 mmol) was added to a solution of the benzoic acid from step B (5.3 g, 17.1 mmol) in methanol (34 mL) at room temperature. The resulting mixture was stirred at reflux overnight. The mixture was allowed to cool to room temperature then concentrated. The resulting residue was dissolved in EtOAc then washed with saturated NaHCO3 (aq), water, then saturated NaCl (aq). The organics were dried over MgSO4, filtered, then concentrated. The resulting residue was purified by silica gel chromatography eluting with 0-10% MeOH/CH2Cl2 to afford the title compound as a white solid. 1H NMR (600 MHz, CDCl3): δ 7.78 (dd, J=5.4, 1.0 Hz, 1H); 3.93 (s, 3H); 0.43 (s, 9H).